I currently have an 8GB M1 running with four users logged in. Three users are iTunes media servers, and the fourth is a regular user.
No heavy computing tasks, obviously, but it's absolutely possible to have more than one user logged in.
Our 286 (which was the first computer my family owned) also had a 40MB Hard Disk, which seemed like plenty at the time. It could run Windows 3.1 with that, although it wasn't exactly fast.
I've done many drugs and many years since then.
I believe that this computer had a 20MB hard drive, and that I eventually ran Stacker to compress the volume and squeeze out a bit more space. I know for sure that I never got anywhere close to 100MB.
On one of my computers in this era, I managed to get a paperwhite VGA and Windows 3.11 (for workgroups) running despite not meeting product specs. My 40-something brain is not quite reliable enough for me to state this with any certainty.